A NEW ROUTE TO THE ASYMMETRIC-SYNTHESIS OF (-)-MALYNGOLIDE AND (-)-EPI-MALYNGOLIDE USING N-SULFONYL-1,3-OXAZOLIDINES AS CHIRAL AUXILIARIES

Authors
WINTER E HOPPE D
Citation
E. Winter et D. Hoppe, A NEW ROUTE TO THE ASYMMETRIC-SYNTHESIS OF (-)-MALYNGOLIDE AND (-)-EPI-MALYNGOLIDE USING N-SULFONYL-1,3-OXAZOLIDINES AS CHIRAL AUXILIARIES, Tetrahedron, 54(35), 1998, pp. 10329-10338
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
35
Year of publication
1998
Pages
10329 - 10338
Database
ISI
SICI code
0040-4020(1998)54:35<10329:ANRTTA>2.0.ZU;2-V
Abstract
(-)-Malyngolide (1), an antibiotically active delta-lactone, and its e pimer 10 were prepared enantioselectively using [2R,2(1S),4R]- and 4R] -4-ethyl-3-(2-nitrobenzenesulfonyl)-2-(1-nonyl- 2-oxocyclopentyl)-1,3- oxazolidine (5a and 5b) as key-intermediates. Furthermore, a new cleav age procedure for the chiral auxiliary is reported. (C) 1998 Elsevier Science Ltd. All rights reserved.